Leonardo DiCaprio’s four-house compound in the Hollywood Hills underwent major renovations

Leonardo DiCaprio’s lavish four property compound in the Hollywood Hills is getting a drastic makeover – with the actor getting the opportunity to acquire a fifth home for his extensive estate.

The Oscar-winner, 48, who is worth an estimated $300 million, has been slowly building up his estate since purchasing his main home for $2.5 million more than two decades ago – a 4,500-square-foot hilltop house in the Bird Streets neighborhood, which boasts jaw-dropping views and an infinity pool.

His main home looks to be undergoing a major renovation, with a digger seen on the patio, a full skip of building materials in the driveway and an empty pool.

The interior also appears to be undergoing a renovation. A building permit recently connected to it states the home is being reroofed to comply with regulations as it is in a Very High Fire Hazard Severity Zone.

DiCaprio first moved into the Oriole Way compound – which is actually two side-by-side properties – in 1994. One of the homes was Madonna’s former digs.

Lavish: Leonardo DiCaprio's lavish four property compound in the Hollywood Hills is getting a drastic makeover - with the actor getting the opportunity to acquire a fifth home for his extensive estate

Lavish: Leonardo DiCaprio’s lavish four property compound in the Hollywood Hills is getting a drastic makeover – with the actor getting the opportunity to acquire a fifth home for his extensive estate

Mogul: The Oscar-winner, 48, who is worth an estimated $300million , has been slowly building up his estate since purchasing his main home for $2.5million more than two decades ago - a 4,500-square-foot hilltop house in the Bird Streets neighborhood, which boasts jaw-dropping views and an infinity pool

Mogul: The Oscar-winner, 48, who is worth an estimated $300million , has been slowly building up his estate since purchasing his main home for $2.5million more than two decades ago – a 4,500-square-foot hilltop house in the Bird Streets neighborhood, which boasts jaw-dropping views and an infinity pool

The 12,530 square foot Hollywood Hills home boasts five bedrooms, eight and a half bathrooms, a screening room, wine cellar and spa. DiCaprio is understood to rent the home out to his actor pals.

In December 2022, the star bought a $10.5million 3,500 square-foot, four bedroom, four bathroom home in the celebrity enclave, Bird Streets of Hollywood Hills – which belonged to his former neighbors, Ron and Joan Linclau – who he famously battled with over a basketball court.

The 1963 home was never publicly listed for sale, with the property located on the northern line of his compound. It boasts a pool and a guest house.

DiCaprio used his cousin Robert Hrtica’s limited liability company to purchase the home.

In 2007 the Linclaus filed a lawsuit claiming to be DiCaprio’s basketball court which he built on his property ‘destabilized and caused significant structural damage to their property.’

DiCaprio argued the issues were sparked by an illegal retaining wall the Linclaus had installed.

The lawsuit would later be settled out of court with the Linclaus and the actor continuing to be next door neighbors.

Last year Joan died aged 90 with her widower Ron selling the home to DiCaprio.

Underway: His main home looks to be undergoing a major renovation, with a digger seen in the patio, a full skip of building material in the driveway and an empty pool

Underway: His main home looks to be undergoing a major renovation, with a digger seen in the patio, a full skip of building material in the driveway and an empty pool

Perfect square: In December 2022, the star bought a $10.5 million 3,500 square-foot, four bedroom, four bathroom home in the celebrity enclave, Bird Streets of Hollywood Hills - which belonged to his former neighbors, Ron and Joan Linclau (pink house seen above) - who he famously battled with over a basketball court

Perfect square: In December 2022, the star bought a $10.5 million 3,500 square-foot, four bedroom, four bathroom home in the celebrity enclave, Bird Streets of Hollywood Hills – which belonged to his former neighbors, Ron and Joan Linclau (pink house seen above) – who he famously battled with over a basketball court

Sprawling: DiCaprio first moved into the Oriole Way compound - which is actually two side-by-side properties - in 1994. One of the homes was Madonna's former digs

Sprawling: DiCaprio first moved into the Oriole Way compound – which is actually two side-by-side properties – in 1994. One of the homes was Madonna’s former digs

So much space: His compound is now a whopping five parcels of land with four properties, adding up to more than five acres, 15 bedrooms and 15,000 square feet of living space

So much space: His compound is now a whopping five parcels of land with four properties, adding up to more than five acres, 15 bedrooms and 15,000 square feet of living space

Superstar digs: The star is currently enjoying a European vacation while renovation is underway

Superstar digs: The star is currently enjoying a European vacation while renovation is underway

Renovation: The 1963 home was never publicly listed for sale, with the property located on the northern line of its compound.  It boasts a pool and a guest house

Renovation: The 1963 home was never publicly listed for sale, with the property located on the northern line of its compound. It boasts a pool and a guest house

The 2003 purchase was a four-bed, six-bath place, then 15 years later in 2018, The Revenant star grabbed the adjacent four-bed, four-bath mansion for $4,850,000.

The actor could now add a fifth property to the compound as another three bed property is on the market for $5.35m and is owned by Scream producer Andrew Rona.

The home, which boasts breathtaking views also features a separate guest unit with full bath sits atop the garage, completing the meticulously designed property.

His compound is now a whopping five parcels of land with four properties, adding up to more than five acres, 15 bedrooms and 15,000 square feet of living space.

The Titanic star is quite the property mogul. As well as his compound, he owns homes across California, in Manhattan and a private island in Belize.

In May 2021 DiCaprio went above and beyond the asking price to purchase Jesse Tyler Ferguson’s Spanish Colonial home in Los Angeles’ Los Feliz neighborhood for $7.1 million.

The Modern Family star and his husband Justin Mikita had previously set the original asking price at $6.995 million in March, according to Dirt.

This marks the second Los Feliz home for DiCaprio after he bought another 1920s-era home from Moby in 2018 for $4.9million.

The Killers Of The Flower Moon star reportedly added the home to his collection in order to make it available to family members, as he’s staying put at his three-house estate in the exclusive Bird Streets area above the Sunset Strip.

DiCaprio’s new home was apparently high in demand, after he exceeded the original asking price of $6.995 million.

It’s also a substantial profit for Ferguson, who only paid $4.6 million when he first originally bought it in 2013.

Sparks: The European holiday comes just days after Gigi Hadid and Leonardo enjoyed yet another evening out with his father and stepmother in London

Glam: Gigi, 28, is pictured in Cannes in May 2023

Sparks: The European holiday comes just days after Gigi Hadid and Leonardo enjoyed yet another evening out with his father and stepmother in London

The house was constructed in 1928 and features four bedrooms and four bathrooms spread out over 5,000 square feet.

His previous Los Feliz acquisition, a Tudor-style home from the 1920s that he bought from Moby in 2018, is currently lived in by the actor’s father, George DiCaprio.

He also owns seaside property, a vacant lot on Paradise Cove in Malibu, that he purchased for $23 million.

The Wolf Of Wall Street Star also has a luxurious desert retreat in Palm Springs where he likes to visit with his celebrity friends.

DiCaprio is bicoastal and also maintains multiple high-priced condos in Manhattan.

Leo’s been pictured on numerous outings while enjoying his Italian holiday in the past week. On Saturday he was seen having lunch in Naples on the Amalfi Coast with his dad and Peggy.

He was also pictured enjoying a late-night stroll around Florence with Tobey over the weekend.

The European holiday comes just days after Gigi Hadid and Leonardo enjoyed yet another evening out with his father and stepmother in London.

The supermodel, 28, and the actor were both seen arriving at the Chiltern Firehouse in London.

It marked their second night out in a row in the capital, after they went for dinner with Leo’s parents at China Tang.

The pair’s romance reportedly fizzled out in February but despite the apparent end to their brief relationship, the two were spotted together multiple times in May and have allegedly been hanging out again recently.

Leonardo has a very close relationship with his father, who separated from the actor’s mother shortly after he was born, and married Peggy Farrar two decades later, in 1995.

By Chiki